CZ20001522A3 - Substituted 2-(2ˆ-pyridyloxy)phenylacetamides, processes of their preparation, preparations in which they are contained and their use - Google Patents

Abstract

Substituted 2- (2-pyridyloxy) phenylacetanides are described of formula I wherein R 1 is fluoro, chloro, methyl or halomethyl, R 2 is fluoro, bromo, C 1-4 -alkyl or halomethyl, and R 3 is hydrogen or one of the meanings for R 2, or R 3 is chloro at position 6 when R 3 is hydrogen, or R 3 is chloro at the 5-position when R 2 is fluoro or ve wherein all of R 1, R 2 and R 3 are each chloro, provided that R 1 is not chlorine when R 2 is trifluoromethyl in the 5-position R3 is hydrogen. The following is a method for preparing these compounds, compositions containing them and uses thereof control of harmful fungi or animal pests.

Description

Substituted 2- (2'-pyridyloxy) phenylacetamides, processes for their preparation, compositions containing them and their use

Technical field

The invention relates to 2- (2'-pyridyloxy) phenylacetamides, processes for their preparation, compositions containing them and their use for controlling (controlling) harmful fungi or animal pests.

BACKGROUND OF THE INVENTION

In EP-A 398 692; EP-A 629 609 and EP-A 760 363 disclose α-phenyl-α-alkoximinoacetamides with heteroaryloxy groups in the ortho position. The compounds described in these applications are suitable for use as crop protection agents against harmful fungi and some of them for use as bactericides.

However, the activity of these compounds is not always entirely satisfactory.

SUMMARY OF THE INVENTION

It is an object of the invention to provide compounds with improved activity.

It has been found that the substituted 2- (2'-pyridyloxy) phenylacetamides of formula (I) meet this objective

(AND)

- '2 in which

R ¹ represents a fluorine atom, a chlorine atom, a methyl group or a halomethyl group,

R ² represents fluorine, bromine, alkyl having 1 to 4 carbon atoms or a halomethyl group, and R ³ represents a hydrogen atom or has one of the meanings

listed for  symbol R ² , or. . * R ² represents atom chlorine in position 6, if R ³ means atom hydrogen, or R ³ represents atom chlorine in position 5, when R ² means atom

fluorine, and a compound in which R ¹ , R ² and R ³ are each a chlorine atom, provided that R ^{1 is} not a chlorine atom when R ² represents a trifluoromethyl group at the 5-position and R ³ represents a hydrogen atom.

Further, the invention of formula (I) and compositions having harmful fungi and fungicidal activity.

discloses methods for preparing compounds using compounds of Formula I and containing them to control (control) animal pests. It is preferred

Compounds of formula I differ from those known from the above applications by substituting a 2-pyridinyloxy group which must be substituted at the 3-position with a radical R ¹ having a particular structure and unsubstituted at the 4-position. improved efficacy against harmful fungi and animal pests.

Compounds of formula I can be obtained by methods similar to those described in ΕΡ-Ά 760 363.

In particular, the compounds of formula (Ia) are obtained by the following synthetic process:.

• · · · · ·

The condensation of the benzyl alcohol of the formula IIa with the 2-halopyridines of the formula IIIa in which Hal represents a halogen atom such as chlorine or bromine is carried out under known conditions (see EP-A 760 363;

EP-A 398,692).

The 2-halopyridines of formula IIIa are either commercially available or can be prepared by methods known in the literature (see US 4,279,913; US 4,491,468; JP-A 58/206 563; J. Org. Chem. (1989) p. 1726); following).

The 2-halopyridines of formula IIIa can also be obtained from the 2-hydroxypyridines of formula IIIb 'by halogenation, for example using phosphorus oxychloride (POCl 3). Halogenation is carried out under known conditions (see Houben-Weyl, Methoden der Organischen Chemie, Vol. 5/3, 4th edition, p. 924 et seq., Thieme Verlag Stuttgart and New York (1962)).

Benzyl alcohol literature and EP-A 398 692).

of the general formula to get it for

Ila is also known from known conditions (cf.

The compounds of the formula Ib are obtained in a particularly advantageous manner via the corresponding esters of the formula IV by the following synthetic procedure:

• · · · · · · · ·

+

The condensation of the benzyl bromide of the formula IIb with the 2-hydroxypyridines of the formula IIIb is carried out under conditions known per se (see DE-A 38 35 028).

Benzyl bromide of the general formula in literature and can be obtained for EP-A 420 091; DE-A 39 17 351). 'lib is also known' from known conditions (see

The 2-hydroxypyridines of formula IIIb are either commercially available or can be obtained by methods similar to those known in the literature. 2-hydroxypyridines; wherein R ³ , R ² or R ³ are trifluoromethyl are preferably obtained from commercially available 2-hydroxypyridine carboxylic acids of formula IIIc by reaction with hydrogen fluoride and sulfur fluoride (see DE-A 3,620,064).

For example, compounds of formula IIIb in which R ¹ represents a trifluoromethyl group are obtained from 2-hydroxypyridine-3-carboxylic acids of formula IIIc by the following reaction:

The 2-hydroxypyridine-3-carboxylic acids of formula IIIc are also known from the literature (see EP-A 225 172; US 4,960,896; US 5,034,531) or can be prepared by methods similar to those of the cited literature.

The amidation of the esters of the general formula IV is preferably carried out in a reaction

- 5 ············································ Known conditions using methylamine (see EP-A 398 692):

(IV)

NH2CH3

-►

(Ib)

Due to their C = N double bonds, the compounds of formula I can be obtained in the preparation as E / Z-isomer mixtures which can be separated into substantially pure individual compounds by conventional means, for example crystallization or chromatographic techniques.

However, if mixtures of isomers are obtained in the synthesis, separation is generally not always necessary, as in some cases the individual isomers may be interchangeable during preparation for use or use (for example, by light, acid or base). Corresponding transformations may also occur after application, in the treatment of plants, for example in a treated plant or in a harmful fungus or animal pest to be controlled.

Regarding the C = N-OCH ₃ double bond, the E-isomers of the compounds of formula I are preferred for their activity (the configuration is based on the OCH ₃ group relative to the CONHCH ₃ group).

In the definitions of symbols in the above formulas, collective terms are used, which generally represent the following substituents:

The term C 1 -C 4 alkyl refers to straight or branched C 1 -C 4 hydrocarbon radicals such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl .

• 0 • 0 0 0 0 ·

The term halomethyl refers to methyl groups in which some or all of the hydrogen atoms may be replaced by halogen atoms, for example, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl and chlorodifluoromethyl.

With respect to the intended use of the compounds of formula T, the following definitions of substituents are particularly preferred, either alone or in combination:

Preference is given to compounds of the formula Ia. wherein R ¹ represents a methyl group.

Likewise particularly preferred are compounds of formula Ia in which R ² is a trifluoromethyl group. ·

Furthermore, compounds of the formula Ia in which R @ ¹ represents fluorine or chlorine are particularly preferred.

Especially preferred are also compounds of formula Ia in which R ¹ is trifluoromethyl.

Furthermore, compounds of the formula Ia in which R @ ¹ is C1 -C4 alkyl are particularly preferred.

Particularly preferred are compounds of formula Ia, in which R ² represents a fluorine or bromine atom.

Further particularly preferred are compounds of formula 1b wherein R ¹ is trifluoromethyl.

Further particularly preferred are compounds of the general formula Ib in which R @ ¹ represents a fluorine or chlorine atom.

Likewise particularly preferred are compounds of formula Ib wherein R ² is a trifluoromethyl group.

In addition, compounds of general interest are particularly preferred

- 7 ttttttt tttttt tttttt tt tttttt tt tttttt tttttt tttttt tttttt tttttt tttttt tttt tt tttt tttt formula Ib wherein R ³ represents a hydrogen atom.

Further particularly preferred are compounds of formula Ib wherein R ² is chlorine and R ³ is hydrogen.

Further preferred compounds of formula I are those in which R @ ¹ is fluorine, chlorine, methyl or trifluoromethyl, R @ ² is fluorine, bromine, C1 -C4 alkyl, carbon or trifluoromethyl and R ³ represents a hydrogen atom or has one of the meanings given for R ² -.

Particularly preferred are the 2- (2'-pyridyloxy) phenylacetamides of the formula Ia, in particular the compounds listed in the table below

AND:

Table A

merge C. R ¹ R ² A-1 methyl trifluoromethyl A-2 fluorine trifluoromethyl A-3 methyl difluoromethyl A-4 fluorine difluoromethyl A-5 ' chlorine difluoromethyl A-6 methyl fluorine A-7 fluorine .fluor A-8 chlorine fluorine A-9 methyl bromine A-10 fluorine bromine A-II chlorine bromine A-12 trifluoromethyl trifluoromethyl

φ φ • · · · · φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ

merge C. R ¹ R ² A-13 trifluoromethyl fluorine A-14 trifluoromethyl bromine A-15 trifluoromethyl methyl A-16 - trifluoromethyl ethyl A-17 trifluoromethyl n-propyl A-18 trifluoromethyl isopropyl A-19 trifluoromethyl n-butyl A-20 trifluoromethyl isobutyl A-21 trifluoromethyl tert-butyl

Among the compounds of formula (1b), in particular, the compounds listed in Table B below are:

conveniently

₃ db)

Table B

merge C. R ¹ R ² R ³ B-l methyl trifluoromethyl H B-2 methyl difluoromethyl H B-3 methyl fluorine H B-4 methyl bromine H B-5 methyl methyl H ' B-6 methyl ethyl H B-7 methyl n-propyl H B-8 methyl isopropyl H B-9 methyl n-butyl H B-10 methyl isobutyl H B-II methyl tert-butyl H

Tt ··· • tt · tttt tttt tt ·· ··· tttttttt tttt ·· tt tt tt «· ·· · • tttttttt tttttttt tt tt ttt tttttttt tttttttt ··· t tttt

merge C. R ¹ R ² R ³ B-12 fluorine trifluoromethyl. H B-13 fluorine difluoromethyl H B-14 fluorine fluorine H B-15 fluorine bromine H B-16 fluorine methyl H B-17 fluorine ethyl · H B-18 fluorine n-propyl H B-19 fluorine isopropyl H B-20 fluorine n-butyl H B-21 fluorine isobutyl H B-22 fluorine tert-butyl H B-23 chlorine trifluoromethyl H B-24 chlorine difluoromethyl H B-25 chlorine fluorine Ή B-26 chlorine bromine H B-27 chlorine methyl H B-28 chlorine ethyl H B-29 chlorine n-propyl H B-30 chlorine isopropyl H B-31 chlorine n-butyl H B-32 chlorine isobutyl H B-33 chlorine · tert-butyl H '

The compounds of formula I are useful as fungicides. They exhibit excellent activity against a wide range of phytopathogenic fungi, in particular from the classes Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically and can be used to protect plants as foliar fungicides and soil-acting fungicides.

The compounds of formula I are particularly suitable for controlling (combating) a wide range of fungi in a variety of crops such as wheat, rice, barley, oats, rice, corn, grass, banana, cotton, soybean, coffee, sugarcane, grapevine, ···· «·« * ·· ··

9 9 9 9 9

9 9 9 9 9 9 9 9 9 9

999 9999999 99 9

9 9 9 9 9

9999 999 9 9 9 9 9 9 9

- 10 different fruit-bearing plants, ornamental plants and various vegetables, such as cucumbers, beans, tomatoes, potatoes and pumpkins, as well as the seeds of such plants.

In particular, these compounds are useful for controlling the following plant diseases:

Alternaria species in vegetables and fruits,

Botrytis cinerea (gray mold) in strawberries, vegetables, ornamental plants and vines,

Cercospora arachidicola at groundnut,

Erysiphe cichoracearum and Sphaerotheca fuliginea in pumpkins, Erysiphe graminis (mildew) in cereals, Fusarium and Verticillium species in a number of plants, Helminthosporium species in cereals, My.cosphaerella species in banana and groundnuts,

Phytophthora infestans in potatoes and tomatoes,

Plasmopara viticola in vines,

Podosphaera leucotricha in apple trees,

Pseudocercosporella herpotríchoides in wheat and barley, Pseudoperonospora species in hops and cucumbers, Puccinia species in cereals,

Pyricularia oryzae for rice, Rhizoctonia species for cotton, rice and lawns,

Septoria nodorum in wheat,

Uncinula necator in grapevine, Ustilago species in cereals and sugar cane, and Venturia species (scab) in apple and pear.

In addition, the compounds of formula I are useful in controlling harmful fungi such as Paecilomyces variotii, in the protection of materials (e.g., wood, paper, dispersions, paints, fibers and fabrics) and in the protection of stored products.

The compounds of the formula I are used in such a way that: 9 9 9 9 9 99 9 99 9 99 9 9 9

9999 9999 99 999 • 999 9999999 99 9

99,999,999

9999 999 999 99 99

The fungi or plants, seeds, materials or soil to be protected from fungal attack are treated with a fungicidally effective amount of the active compounds. Application can be carried out both before and after infection of materials, plants or seeds with fungi.

Fungicidal compositions generally comprise from. 0.1 to 95 wt.%, Preferably from 0.5 to 90 wt. of the active compound.

When used for crop protection, the application rates, depending on the effect desired, range from 0.01 to 2.0 kg of active compound per hectare.

For seed treatment, the amount required is generally from 0.001 to 0.1 g, preferably from 0.01 to 0.05. g of active compound per kg of seed.

When used to protect materials or stored products, the application rate of the active compound depends on the nature of the art in which the application is carried out and the desired effect. Typical application rates for the protection of materials are, for example, from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active compound per cubic meter of material to be treated.

The compounds of formula I are also suitable for the effective control of animal pests of the insect, arachnid and nematode classes. They can be used in crop protection a. In the hygiene sector, in the protection of materials and in the veterinary sector for the control of animal pests. .They are particularly suitable for the control of the following animal pests:

butterflies (Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Chacobacteria viridis, Croisella, Chorisella, Choristoneura , Dendroíimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Early Insulation, Early Insulation · · ···························

- 12 Elasmopalpus lignosellus, E-upoecilia ambiguella, Eetria bouliana, Feltia subterranea, Galleria. mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis viresceijs, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Leucocoptera scapula, Leucoclala, Laphyglala, Lapesia , Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata ,. Ostrichia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia ssp. Spodoptera littoralis, Spodoptera. litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, and Zeiraphera canadensis, from the order of the beetles (Coleoptera), e.g. undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata ,. Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis ,. Diabrotica 12-punctata, Diabrotica virififera, Epilachna. varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, MelissushopeSesetholisus, orissophilusSoryzolusis origophilus Ortiorrhynchus sulcatus, • to ··· ················································· · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · To ·

Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola; Phyllotreta nemorum; ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus oleae, Goslinsis brassica, Gasteria canalis, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia scurf, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musea domestica, Muscina stabulans, Oestrus ovis, Phytograss, Phegia, coarctata, Rhagoletis

Frankliniella tritici, Thrips palmi and Thrips'

Tabanus bovinus, Tipula

Atta texana, Monomorium

Hoplocampa pharaonis, cerasi, Rhagoletis pomonella, oleracea, and Tipula paludosa, of the order Thysanoptera, such as Frankliniella fusca, Frankliniella occidentalis,

Scirtothrips citri, Thrips oryzae, tabaci, Hymenoptera, for example Athalia rosae, Atta cephalotes, Atta, sexdens, minute, Hoplocampa testudinea,

Solenopsis geminata and Solenopsis invicta, of the order Heteroptera, for example Acosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Eurysgaster integriceps, Euschistus impictiventris, Leptususisusgylus, Leptususisus phyll. , Solubea insularis and Thyanta.perditor, from the order of the Homoptera, for example Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, ** · 4 · ···

• · · ···· · · ·. • · · · ·

Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphula radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum eume, Macrosiphum avenae , Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla small, Psylla piri, Rhopalomyzus ascalonicus, Rhapalosiphum maidis, Sappaphis mala, Schizaphis graminum, Schizialura lanuginus, Trisoneura lanuginosa, for example Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis, of the order Orthoptera, for example Acheta domestica, Blatta. orientalis, Blattella germanica, Forficula auricularia, Gryllothalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur rubrum, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciana, spider mites such as Acarina mites, for example Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpum, ricinus, Ixodes rubicundus, Ornithodorus Moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes. ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, and Tetranychus urticae, and · · · · · · · · · · · · To · to · to · to · to · to · to · tototo tototo ·· ·

- 15 nematodes such as root knot nematodes, for example Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst nematodes such as Globodera rostochienšis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera schachtii, Heterodera schachtus, Ditylenchus destructor, Ditylenchus dipsaci, Helicocylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus penitlenisus, Pratylenchus penetatytus.

When controlling animal pests in field conditions, the application rate of the active compound is from 0.1 to 2.0 kg / ha, preferably from 0.2 to 1.0 kg / ha.

Conventional compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules, can be prepared from the compounds of formula (I). The dosage form depends on the particular intended use, but in any case should guarantee an accurate and uniform distribution of the compound of the invention.

The compositions are prepared in a manner known per se, for example by mixing the active compound with solvents and / or carriers, if desired using emulsifiers and dispersants, while other organic solvents may also be used as co-solvents when the diluent is water. Suitable excipients are mainly solvents such as. aromatic solvents (eg xylene), chlorinated aromatic solvents (eg chlorobenzenes), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol), ketones (eg cyclohexanones), amines (eg ethanolamine, dimethylformamide) and water; carriers such as ground natural, minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxy-

tttttt · tttttttt · 4 4 9 4

44 ’4

44 * tttt tt 4 4 4

4 ’4 9

Fatty alcohol ethylene ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquids and methylcellulose.

Suitable surfactants are the alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, alkali metal sulfates and fatty acid sulfates and their fatty acid sulfates alkaline earth metals, salts of glycol ethers of sulfated fatty alcohols, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde; , alkyl aryl polyether alcohols, isotridecyl alcohol, fatty alcohol condensates. with ethylene oxide, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol-polyglycol ether acetal, sorbitol esters, lignosulfite waste liquids and methylcellulose.

Medium to high boiling oil fractions such as kerosene or diesel fuel, coal tar and vegetable or animal oils, aliphatic, cyclic and aromatic hydrocarbons are suitable for the direct spraying of suitable solutions, emulsions, pastes or oil dispersions. , for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents such as dimethylformamide, dimethylsulfoxide, N- methylpyrrolidone and water.

Powders, spreading agents and dusts can be prepared by mixing or grinding the active ingredients with>.

φ ···

- 17 solid support.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are, for example, mineral soils such as silica, silica, silica, silicates, talc, kaolin, attapulgite, limestone, lime, chalk, earth clay, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and plant origin products such as cereal flour, tree bark flour, wood flour and nut shell flour, cellulose powders and other solid carriers. .

The compositions generally contain from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound. The active compounds are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

Examples of formulation are:

I. 5 parts by weight of a compound according to the invention are mixed intimately with 95 parts by weight of finely divided kaolin. A dust containing 5 wt. of the active compound.

II. 30 parts by weight of the compound of the invention are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of the silica gel. This provides a composition comprising the active compound having good adhesive properties (active compound content 23% by weight).

III. 10 parts by weight of a compound of the invention are dissolved in a mixture containing 90 parts by weight of xylene, 6 parts by weight of the addition product of 8 to 10%.

0000 ···

18 moles of ethylene oxide with 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonate and 2 parts by weight of the addition product of 40 moles of ethylene oxide with 1 mol of castor oil (9% by weight of active compound).

IV. 20 parts by weight of a compound of the invention are dissolved in a mixture comprising 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of an adduct of 7 moles of ethylene oxide with 1 mol of isooctylphenol and 5 parts by weight of an adduct of 40 moles of ethylene oxide with 1 mol of castor oil. compound is 16 wt%).

V. 80 parts by weight of the compound of the invention are mixed intimately with 3 parts by weight of sodium diisobutylnaphthalene-α-sulfonate, 10 parts by weight of sodium lignosulfone. acid from sulfite waste liquid and 7 parts by weight of silica gel powder and the mixture is ground in a hammer mill (80% by weight of active compound).

VI. 90 parts by weight of a compound of the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone to give a solution suitable for use as very small droplets (the active compound content is 90% by weight).

VII. 20 parts by weight of a compound of the invention are dissolved in a mixture containing 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of an adduct of 7 moles of ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight of an adduct of 40 moles of ethylene oxide with 1 mol of castor oil. The solution is poured into 100,000 parts by weight of water and gently dispersed therein to give an aqueous dispersion containing 0.02% by weight. of the active compound.

• · · · · · · · · · • * · · * * * * * * * * * * * * * · · · · · · · · · · · · ·

VIII. 20 parts by weight of the compound of the invention are intimately mixed with 3 parts by weight of diisobutylnaphthalene-α-sulfonate in sodium, 17 parts by weight of sodium lignosulfonic acid from a sulphite waste liquid and 60 parts by weight of powdered silica gel, and ground in a hammer mill. The mixture is gently dispersed in 20,000 parts by weight of water to give a spray liquid containing 0.1% by weight of water.

of the active compound.

The active compounds may be administered as such, in the form of compositions containing them, or in dosage forms prepared therefrom, for example in the form of solutions for _; direct spraying, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, spreading agents or granules, by means of spraying, atomization, spraying, spreading or potting. The dosage forms depend entirely on the intended uses, but in any case should ensure the finest possible distribution of the active compounds according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the active compounds, as such or dissolved in an oil or solvent, can be homogenized in water using a wetting agent, binder, dispersant or emulsifier. Alternatively, concentrates containing the active compound, wetting agent, binder, dispersant or emulsifier and optionally a solvent or oil may be prepared, which concentrates are suitable for dilution with water.

The concentrations of the active compound in ready-to-use preparations can be varied within a wide range. They are generally from 0.0001 to 10%, preferably from 0.01 to 1%.

«· · · · · · · · · ·

ft * · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · ·

The active compounds can also be successfully used by the ultra-low volume process (ULV), with compositions containing more than 95% by weight of active compound. the active compound or even the active compound without additives.

Oils of various types, herbicides, fungicides, other pesticides or bactericides can be mixed with the active compounds. if necessary, just immediately before application (tank mix). These agents may be mixed with the compositions of the invention in a weight ratio of from 1:10 to 10: 1.

The compounds of the invention may also be present in the form for use as fungicides with other active compounds, for example herbicides, insecticides, growth regulators, fungicides or also with fertilizers. In many cases, compounds of the formula I or compositions containing them, when in a form for use as fungicides, are mixed with other fungicides, resulting in a broadening of the fungicidal spectrum of activity.

The following list of fungicides with which the compounds of the invention may be used illustrates possible combinations, but is not limited thereto.

sulfur, dithiocarbamates and derivatives thereof such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, ethylene bisdithiocarbamate. zinc, manganese zinc ethylenebisdithiocarbamate, manganese zinc ethylenediaminobisdithiocarbamate, tetramethylthiuram disulfides, zinc N-N-ethylenebis dithiocarbamate complex, zinc ammonium β, N'-propylenebisate disinate, thiocarbamoyl disulfide;

nitro derivatives such as dinitro (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethyl-acrylate, 2-sec-butyl-4,6-dinitrophenylisopropyl carbonate , diisopropyl- 21 I ···· tttt · · · «

-5-nitroisophthalate;

heterocyclic compounds such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine; O, O-diethylphthalimidophosphonothioate, 5-amino-1- [bis (dimethylamino) phosphinyl) -3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio- 1,3-dithiolo [4,5-b] quinoxaline, methyl 1- (butylcarbamoyl) -2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2- (2-furyl) benzimidazole, 2- (4-thiazolyl) benzimidazole, N- (1,1,2,2-tetrachloroethylthio) tetrahydrophthalimide. N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide,

N-dichlorofluoromethylphthio-N ', N'-dimethyl-N-phenylsulfodiamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene,

4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone, pyridine-2-thiol-1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1 4-oxathiine, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-ol

-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl-2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5 Dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, -N-formyl-N-morpholine-2,2,2-trichlorethylacetal, piperazine-1,4-diylbis - (1- (2,2,2,2) -trichloroethyl) formamide,

formylamino-2,2,2-trichloroethane, morpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts. N- [3- (tert-butylphenyl) -2-methylpropyl] -cis-2,6-dimethylmorpholine, N- [3- (p-tert-butylphenyl) -2-methylpropyl] piperidine, 1- [2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-ylethyl] -1H-1,2,4-triazole, 1- [2- (2,4-dichlorophenyl) -4-n- propyl-1,3-dioxolan-2-ylethyl] -1H-1,2,4-triazole, N- (n-propyl) -N- (2,4,6-trichlorophenoxyethyl) -N 'imidazolylurea, 1- (4-Chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butyl- (3,4-dichloroanilino) -12,6-dimethyl-N- tridecyl «· · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · ·

22-tannone, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol, (2RS, 3RS) -1- [3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-ylmethyl] -1H-1,2,4-triazole, α- (2-chlorophenyl) -a- (4-chlorophenyl) -5 - pyrimidine-methanol, 5-butyl-, 2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis (p-chlorophenyl) -3-pyridine-methanol, 1,2-bis- (3-ethoxycarbonyl-2-thioureido) benzene, 1, 2-bis- (3-methoxycarbonyl-2-thioureido) benzene, strobilurines such as methyl-ε-methoxyimino- [α- (o-tolyloxy) -o-tolyl] acetate, methyl-E-2- {2- [ 6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate, methyl E-methoxyimino [α- (2-phenoxyphenyl)] acetamide, methyl E-methoxyimino- [α- (2, 5-dimethylphenoxy) -o-tolyl] acetamide, anilhopyrimidines such as N- (4,6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] ] aniline, N- [4-methyl-6-cyclopropylpyrimidin-2-yl] aniline, phenylpyrrols such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile. cinnamides such as 3- (4-chlorophenyl) -3- (3,4-dimethox) yphenyl) acryloylmorpholine, and a number of other fungicides such as dodecylguanidine acetate, 3 '- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene,. methyl N- (2,6-dimethylphenyl) -N- (2-furoyl) -DL-alaninate, DL-N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) alanine methyl ester, N- ( 2,6-dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone, methyl DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester, 5-methyl-5-vinyl-3 ^_ ( 3,5-dichlorophenyl) -2,4-dioxo-1,3-oxazolidine, 3- [3,5-dichlorophenyl (-5-methyl-5-methoxymethyl) -1,3-oxazolidine-2,4-dione, 3- (3,5-dichlorophenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano- [N- (ethylaminocarbonyl) -2-methoximino] acetamide, 1- [2- (2,4-dichlorophenyl) pentyl] -1H-1,2,4-triazole, 2,4-difluoro-α- (1H-1,2,4-triazolyl-1-methyl) ) benzhydryl alcohol, N- (3-chloro-2,6-dinitrile)

23- (4-trifluoromethylphenyl) -5-trifluoromethyl-3-chloro-2-aminopyridine, 1 - ((bis- (4-fluorophenyl) methylsilyl) methyl) -1H-1,2,4-triazole.

DETAILED DESCRIPTION OF THE INVENTION

Synthesis examples

The procedures described below in the synthesis examples, with corresponding modification of the starting materials, were. The resulting compounds are listed in the table following the examples, together with physical data.

Example 1

Preparation of α-anti-methoxyimino-N-methyl-2- (3-fluoro-5-trifluoromethyl-2-pyridyloxy) methylphenylacetamide (Compound No. 1-1)

nhch ₃

A suspension of 1.4 g of sodium hydride in 15 ml of dimethylformamide is mixed with a solution of 11.1 g of (E) -2- [2- (hydroxymethyl) phenyl] -2-methoxyimino-N-methylacetamide in 12 ml of dimethylformamide. The reaction mixture is sonicated for about 10 minutes and then stirred for 1 hour at about 20-25 ° C. A solution of 9.2 g of 2,3-difluoro-5-trifluoromethylpyridine in 85 ml of dimethylformamide is added dropwise. and the mixture is stirred for about 24 hours at 22-25 ° C. The reaction mixture is taken up in 1 L of dilute sodium chloride solution and extracted with methyl tert-butyl ether. The combined organic phases are washed with water and dried. The solvent is distilled off under reduced «« ·· »·

0

0 0 0

0 • 0

0

The residue was chromatographed on silica gel using cyclohexane / methyl tert-butyl ether (2: 1) as eluent to give 6.9 g of the title compound as a light powder, m.p. 112-116 ° C. . '

Infrared (cm ^-1 ): 3380, 1659, 1623, 1498, 1453,

1336, 1272, 1151, 1131, 1040 '

Example 2

Preparation of 2-chloro-3-methyl-5-iodopyridine

CH

Cl

To a suspension of 146 g of 10% (w / w) hydrochloric acid and 23.4 g of 2-amino-3-methyl-5-iodopyridine (J. Org. Chem. (1995), p. 5356) is added at -10 ° C. it adds 21.3 g of chlorine gas. A solution of 48.3 g of sodium nitrite in 120 ml of water is then added dropwise at -5 ° C. After stirring at 0 ° C for about 2 hours, the mixture was diluted with 1 L of water and extracted with methyl tert-butyl ether. The organic phase was washed with sodium bicarbonate solution and water and then dried. The solvent was removed by distillation under reduced pressure and the residue was chromatographed on silica gel using cyclohexane / methyl tert-butyl ether 1:10 as eluent to give 3.6 g of the product as dark crystals.

‘H-NMR (CDCl 3): δ values in ppm = 8.4. (1H), 7.9 (1H), 2.3 (3H)

94

4 4 *

4 9 · * · _ ···· * and ·, i ». ·. ·· ··· «··· ·· * **

- 25 Example 3

Preparation of 2-chloro-3-methyl-5-trifluoromethylpyridine

CH,

A solution of 84.7 µg of the pyridine derivative of Example 2 in 1 L of N-methylpyrrolidone was mixed with 136.3 g of sodium trifluoroacetate and 95.2 g of copper iodide, and the mixture was stirred at 160 ° C for 2 hours. After cooling, the mixture was taken up in about 3 L of water and extracted with ethyl acetate. The combined organic phases were washed with 2.5% (wt.) Aqueous ammonia solution and dried, and then _x is freed from solvent under vacuum. From the remaining crude product, after rectification on a short column, 14.3 g of the title compound is obtained, b.p. 70-75 ° C (2.5 kPa) in a colorless oil.

and water, reduced form

Ή-NMR (CDCl 3): δ values in ppm-8.6 (1H), 7.8 (1H), 2.4 (3H)

Example 4

Preparation of α-anti-methoxyimino-N-methyl-2- (3-methyl-5-trifluoromethyl-2-pyridyloxy) methylphenylacetamide (Compound No. 1-2)

nhch ₃

A solution of 23.8 g of (E) -2- [2- (hydroxymethyl) phenyl] -2-methoxyimino-N-methylacetamide in 200 ml of dimethylformamide is mixed with a suspension of 2.82 g of sodium hydride in 25 ml of dimethylformamide.

· Tot oto oto oto oto to to • • • to...

· · To to to to to

The reaction mixture is sonicated for about 10 minutes and then stirred for 1 hour at 20-25 ° C. A solution of 20.9 g of 2-chloro-3-methyl-5-trifluoromethylpyridine (z) is added dropwise. of Example 3) in 150 ml of dimethylformamide and stirred for 3 hours at 45 ° C and for an additional 24 hours at 22-25 ° C. The reaction mixture is taken up in 3 L of dilute sodium chloride solution and extracted with methyl tert-butyl ether. . The combined organic phases are washed with water, dried and freed from solvent under reduced pressure. The residue is chromatographed on silica gel using cyclohexane / methyl tert-butyl ether (1: 1) as eluent to give 15.8 g of the title compound. 133-135 ° C.

Infrared spectrum 1264, 1173, cm‘j: 1672, 1418, 1335, 1324, 1269, 1123, 1038 Table I

merge C. general formula R ¹ R ² R ³ physical data (melting point, in ° C; infrared spectrum in cm ^-1 ) 1-1 la F cf ₃ 110-112 1-2 la ch ₃ cf ₃ - 125-130 1-3 [0057] Ib cf ₃ Cl H 103-105

«· ·

4 4

449

4 ·

···· · * ·

4

9 4

4 4 9

4 444

4 9

4

merge C. general formula R ¹ R ² R ³ physical data (melting point in ° C; infrared spectrum in cm ¹ ) 1-4 [0057] Ib ch ₃ ch ₃ H 116-118 1-5 [0057] Ib Cl Cl Cl 147-148 1-6 Ib Cl Cl cf ₃ . 139-141 1-7 [0057] Ib Cl F cf ₃ 108-111 1-8 Ia Cl CHF ₂ 1669, 1605, 1474, 1352, 1069, 1036, 988

Examples of efficacy against harmful fungi

The fungicidal activity of the compounds of formula I is demonstrated by the following experiments:

The active compounds, individually or together, were formulated as a 10 wt.% Emulsion in a 70 wt. % cyclohexanone, 20 wt. % Nekanil® LN (Lutensol® AP6, emulsifying and dispersing wetting agent, based on ethoxylated alkylphenols) and 10 wt. Wettol® EM (non-ionic emulsifier based on ethoxylated castor oil) and diluted with water to the desired concentration.

Compounds known from EP-A 398 692 (Table 7, No. 78; Compound A) and

EP-A 760,363 (No. 9; Compound B):

·· ···· ♦ · *

·· * «

999

9 • · · · ·

9

9 9

9

99 • · β 9

9 9 9

9 9 9

9 9 9

99

- 28 Application example 1

Effectiveness against Plasmopara viticola

Muller-Thurgau vine leaves grown in a pot are sprayed with an aqueous preparation of the active compound prepared from a stock solution containing 10% active compound, 63% cyclohexanone and 27% emulsifier until the leaves are wet by spraying. The Tiby was able to evaluate the long-term efficacy of the compounds, leaving the plants in the greenhouse after spraying for 7 days. Only then are the plants inoculated with an aqueous suspension of Plasmopara viticola. Then, the vine plants were first placed in a 24 ° C steam saturated air chamber for 48 hours and then in a greenhouse at 20 ° C for 5 days. The plants are then placed in a high humidity chamber for a further 16 hours to promote the formation of sporangiophores. The extent of fungal infection on the undersides of the leaves is then evaluated visually.

In this test, plants treated with Compounds Nos. 1-1, 1-2, 1-3, 1-5, 1-6, 1-7, and 1-8 at a concentration of 4 ppm showed an infection of no more than 15%, whereas plants treated with Comparative Compounds A and B at a concentration of 4 ppm showed infection of 60% and 50%, respectively, and untreated plants showed infection of 75%.

Example of use 2

Long-term efficacy against Phytophthora infestans on tomatoes

Tomato plants. varieties grown in a pot of GroBe Fleischtornáte are sprayed in a 4-leaf stage with an aqueous suspension prepared from a stock solution containing 10% active compound, 63% cyclohexanone and 27% emulsifier. the leaves are wet so that spraying occurs. In order to evaluate the long-term efficacy of the compounds, the leaves are infected with an aqueous suspension of zoospores of Phytophthora to this.

to one day after application of the active compound. Thereafter, the plants are first placed in a chamber with air saturated with water vapor at a temperature of 16 to 18 ° C. After 6 days, the potato fungus on untreated but infected control plants develops to such an extent that the infection can be visually determined as a percentage.

In this test, plants treated with Compounds Nos. 1-1, 1-2, 1-5, 1-6, 1-7 and 1-8 at 16 ppm showed an infection of no more than 15%, whereas plants treated with Comparative Compounds A and B in at a concentration of 16 ppm showed an infection of 25% and 100%, respectively, and untreated plants showed an infection of 100%.

Application example 3

Activity against Puccinia recondita (wheat rust) on wheat

The leaves of the Fruhgold wheat seedlings grown in a pot are dusted with spores of wheat rust (Puccinia recondita). The plant pots are then placed in a high atmospheric humidity (90-95%) chamber at 20-22 ° C for 24 hours. During this time, the spores germinate and the germinating fungus penetrates into the leaf tissue. The next day, the infected plants are sprayed with an aqueous formulation of the active compound prepared from a stock solution containing 10% active compound, 63% cyclohexanone and 27% emulsifier until spraying occurs. After spraying has dried, the test plants are cultivated for 7 days in a greenhouse at a temperature of 20-22 ° C and a relative atmospheric humidity of 65-70%. The extent of fungal development on the leaves is then determined.

In this test, plants treated with Compounds Nos. 1-1, 1-2, 1-3, 1-6 and 1-8 at 16 ppm showed an infection of no more than 15% and plants treated with Compounds Nos. 1-1, 1-2, 1-3, 1-6 and 1-8 at 63 ppm showed no infection, whereas plants treated with Comparative Compound A v

»Φ φφ φ φ φ φ φφφ φ

φ φ

φ φ φ · · · · ·......... · Φ · · φ φ φ φφ φ

- 30 concentrations of 16 ppm and 63 ppm showed 75% and 40% infection respectively, and untreated plants showed infection

%.

Application example 4

Activity against Pyricularia oryzae (protective action)

The potted leaves of the Tai-Nong 67 rice seedlings are sprayed with an aqueous formulation of the active compound prepared from a stock solution containing 10% active compound, 63% cyclohexanone and 27% emulsifiers until the leaves are wet by flowing spraying. The next day the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The test plants are then placed for 6 days in an air-conditioned chamber at 22-24 ° C and 95-99% relative humidity. The extent of the disease on the leaves is then visually determined.

In this test, plants treated with Compounds Nos. 1-1, 1-2, 1-3, 1-5, and 1-8 at 63 ppm showed an infection of at most 15% and plants treated with Compounds Nos. 1-1, 1-2,

1-3, 1-5 and 1-8 at a concentration of 16 ppm infection at most 40% while the plants' treated. Comparative Compound A at a concentration of 63 ppm and 16 ppm showed an infection of 60% and 90%, respectively, and untreated plants also showed an infection of 90%.

Examples of efficacy against animal pests

The following experiments demonstrate the efficacy of compounds of formula I in animal pests:

The active compounds are formulated:

as a 0,1% solution in acetone; or

b. as a 10% emulsion in a 70 wt. % cyclohexanone, wt. of Nekanil® LN (Lutensol® AP6, • to

• toto * * to to to - - - - -

% surfactant with emulsifying and dispersing effects, based on ethoxylated alkylphenols) and 10 wt. of Wettol® EM (a non-ionic emulsifier based on ethoxylated castor oil) and diluted to a desired concentration with a. acetone and b.

At the end of the experiments, the lowest concentrations were determined in each case at which compounds still caused 80-100% inhibition or mortality compared to untreated control experiments (critical or minimum concentration).

Example 1

Efficacy against Nephotettix cincticeps, contact efficacy

1 ml of an aqueous preparation containing the active compounds was applied to 9 cm diameter filter paper dishes and subsequently placed in 5 adult Nephotettix cincticeps individuals. Mortality was determined after 24 hours.

In this test, the active compound 1-2 exhibited a critical concentration of 0.2 mg, while the comparative active compounds A and B showed a critical concentration of more than 0.2 mg.

Claims (12)

PATENT CLAIMS 1. Substituted 2- (2'-Pyridyloxy) phenylacetamide of the general formula I in which R ¹ represents a fluorine atom, a chlorine atom, a methyl group or a halomethyl group, R ² represents fluorine, bromine, alkyl having 1 to 4 carbon atoms or halomethyl, and R ³ represents a hydrogen atom or has one of the meanings given for R¹ ² or · R ² represents a chlorine atom in position 6 when R ³ represents a hydrogen atom, or R ³ represents a chlorine atom in the 5-position when R ² represents a fluorine atom or in which all the symbols R ¹ , R ² and R ³ each represent a chlorine atom, provided that R ¹ does not represent a 'chlorine atom' when R ² represents' the trifluoromethyl group at the 5-position and R ³ represents a hydrogen atom. Phenylacetamide according to claim 1 General formula Ia nhch ₃ • ft • ft 9999 9 9 9 9 9 · ftft ftft ftft ftft ftft ft ft ft ft ft ft ft ft Wherein R ¹ and R ² are as defined in claim 1. A phenylacetamide of formula Ia according to claim 2, wherein R ¹ is methyl or trifluoromethyl and R ² is as defined in claim 1. The phenylacetamide of formula Ia according to claim 2, wherein one of the radicals R ¹ and R ² represents a methyl group and the other one represents a trifluoromethyl group. Fifth phenylacetamide according to claim 1 of formula Ib db) in which R ^1, R ² and R ³ are as defined in claim 1. '. . The phenylacetamide of formula 1b according to claim 5, wherein R ¹ represents a trifluoromethyl group, R ³ represents a hydrogen atom and R ² is as defined in claim 1. A process for the preparation of phenylacetamides of the formula Ta according to claim 2, characterized in that the benzyl alcohol of the formula IIIa is reacted under basic conditions with 2-halogenopyridine of the formula IIIa. · · To · to to to to to to to to to to to to to to to to to to... · ·· · ··· • to ·· this Hal (IIIa) in which Hal represents a halogen atom and the remaining general symbols have the meanings defined for formula I in the claim 1. A process for the preparation of phenylacetamides of the formula Ib according to claim 5, characterized in that the benzyl bromide of the formula IIb (Hb) is reacted under basic conditions with a 2-hydroxypyridine of the formula IIIb. of claim 1, to form 2- (2'-pyridyloxy) phenylacetate of the general formula IV (IV) in which the individual symbols have the meanings defined for ftft. The compound of formula I in claim 1, and 2- (2'-pyridyloxy) phenylacetate of formula IV is reacted with methylamine to form a phenylacetamide of formula Ib. 9. A composition suitable for controlling animal pests or harmful fungi, characterized by. comprising a solid or liquid carrier and an effective amount of at least one phenylacetamide of formula I according to claim ¹ ; Use of a phenylacetamide of the formula I according to claim 1 for the preparation of a composition suitable for controlling animal pests or harmful fungi. A method for controlling harmful fungi, characterized in that the fungi or materials, plants, soil or seeds to be protected against fungal attack are treated with an effective amount of at least one phenylacetamide of the formula I according to claim 1. 12. A method of controlling animal pests comprising treating the animal pests or materials, plants, soil or seeds to be protected therefrom with an effective amount of a phenylacetamide of the formula I as claimed in claim 1.